Just a quickie here. To make any sort of sweeping judgment one way or another about what to do in leagues is always dangerous, it’s never black and white and circumstances change. That’s why you often the first part of any answer in a chat of fantasy baseball questions be: “it depends”. One such area is extending pitchers. It, too, lives in the gray, but I’d say it is closer to the definitive are than other rules. Extending pitcher contracts is rarely a great idea, though it can still be a good one, just one rife with risk. Now before you email me citing your offensive player extension that went awry because of injury, let me be clear that I’m aware of the fact that every player carries risk of getting hurt. That’s just the nature of sports.

However, you cannot deny that there is heightened risk with starting pitchers and knowingly assuming that risk isn’t always a good idea. Even the most rock solid guys can turn at the drop of a hat. Consider these three recent cases. Let’s start at the low-end where the breakdown wasn’t an overwhelming shock if only because of his age. Roy Halladay was coming off six straight amazingly strong seasons during which he went at least 220 innings and averaged 236. There was no way he was on anyone’s roster at a cheap price this time last year, but he might’ve been at a fair price once you factor inflation leading some to hang onto him thinking it was as safe as can be for a pitcher. He was kept in one of my NL-Only leagues for a mid-$30s cost when he’d have easily gone north of $40. We know how it turned out. He looked human for the first time since 2004 pitching just 156.3 innings and posting a 4.49 ERA. Now at 36, he’s going at a discounted rate as if 2012 is the new norm and his previously insane track record of awesomeness is but a memory.

Next up is Dan Haren heading into the 10th year of his career, he too wasn’t on anyone’s roster for $15 dollars or anything, but coming off of his 2010 where he had a 3.91 ERA, he came at a discount in 2011 drafts making him someone who was likely below market in many leagues and could be another guy who you keep just to avoid any inflation in the auction. He’d made 33 starts a year or more for seven straight seasons including 34 four times and even 35 once. He averaged 226 innings during the stretch with an excellent set of base skills. His workhorse reputation led me to say this in 2012’s pitching guide:

He remains one of the most rock solid pitchers in all of baseball with no fewer than 216 innings since 2005 and increasing workloads yearly since 2008 topping out at last year’s 238.

Whoops. A balky back proved too difficult to pitch through and he went just 176.7 innings with stretches of ugliness that led to a 4.33 ERA. We saw runs of the brilliant Haren, too, but not enough to cancel the bad. No one is immune.

And the most disastrous of them all whose retirement actually prompted the idea to discuss this a while back: Brandon Webb. If there was one thing you could rely on Webb for it was innings and good ones at that. He struggled with walks in his second season leading to an ugly 1.51 WHIP, but his 3.59 ERA was still pretty solid and proved to be the worst of his career (not counting the 13.50 in his 4-inning swan song “season” of 2009). Starting in 2004 he went 208, 229, 235, 236.3, and 226.7. All before 30 years old.

Just keep these three cases (and many, many more) in mind this winter when you are deciding on your keeper lists. The more pitchers you have, the more risk you’re assuming. Again, this doesn’t mean that you should cut your $3 R.A. Dickeyloose or not give Chris Sale a contract for 2013. But start thinking long and hard about extensions to pitchers. How many years do you want to commit to Sale beyond this one? Say you had him at $1 because he used to be a reliever, but now he’s due up for a contract at $5 per year.

Sure, $16 sounds plenty reasonable because he’d sure as hell go for more than that this year in the auction, but now you’re betting on 2013, 2014, and 2015. Just go $6 and enjoy the crazy value this year (assuming he’s stay upright of course) and work on finding the next Sale. How many of your are in the midst of Brandon Beachy or Cory Luebke contracts? This goes double for leagues where they let you out of contracts if they go sour, but charge penalties to do so. Those of you enjoying a David Price contract should be very thankful. It has worked out brilliantly. It’s the exception.

Go back and look through top prospects lists and see how many guys didn’t work out as panned and try to recall some of the trades you made to earn their rights. Again, there is risk throughout our game, but the point is to minimize how much you can incur. Extending a pitching beyond the upcoming year is the easiest way to get a double serving of risk you thought you were ordering.

OK, that wasn’t as quick as I thought. I tend to get going sometimes and end up much longer winded than anticipated.